Preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs, via resolution of precursors

Tetrahedron Asymmetry

Volumn 14, Issue 3, 2003, Pages 381-387

  Caro, Yolanda ^a   Masaguer, Christian F ^a   Raviña, Enrique ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

(4 OXO 1,2,3,4 TETRAHYDRONAPHTHALEN 2 YL)METHYL 4 METHYLBENZENESULFONATE; BUTYROPHENONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CENTRAL NERVOUS SYSTEM; CYCLIZATION; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; PRECURSOR; PRIORITY JOURNAL; STOBBE CONDENSATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037423125     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00822-4     Document Type: Article

References (29)

1. Hartman D.S., Civelli O. Prog. Drug Res. 48:1997;173-194.
2. Hoyer D., Clarke D.E., Fozard J.R., Hartig P.R., Martin G.R., Mylecharane E.J., Saxena P.R., Humphrey P.P. Pharmacol. Rev. 46:1994;157-203.
3. Uphouse L. Neurosci. Biobehav. Rev. 21:1997;679-698.
4. Cowen P.J. Br. J. Psychiatry Suppl. 1991;7-14.
5. Roth B.L., Willins D.L., Kristiansen K., Kroeze W.K. Pharmacol. Ther. 79:1998;231-257.
6. Prisco S., Pagannone S., Esposito E. J. Pharmacol. Exp. Ther. 271:1994;83-90.
7. Iyer R.N., Bradberry C.W. J. Pharmacol. Exp. Ther. 277:1996;40-47.
8. Holstein A.P., Chen C.H. Am. J. Psychiatry. 122:1965;462-463.
9. King D.J. Eur. Neuropsychopharmacol. 8:1998;33-42.
10. Capuano B., Crosby I.T., Lloyd E.J. Curr. Med. Chem. 9:2002;521-548.
11. Ravina E., Masaguer C.F. Curr. Med. Chem.: Central Nervous System Agents. 1:2001;43-62.
12. Cortizo L., Santana L., Ravina E., Orallo F., Fontenla J.A., Castro E., Calleja J.M., De Ceballos M.L. J. Med. Chem. 34:1991;2242-2247.
13. Loza M., Verde I., Castro M.E., Orallo F., Fontenla J.A., Calleja J.M., Ravina E., Cortizo L., De Ceballos M.L. Bioorg. Med. Chem. Lett. 1:1991;717-720.
14. Brea J., Rodrigo J., Carrieri A., Sanz F., Cadavid M.I., Enguix M.J., Villazón M., Mengod G., Caro Y., Masaguer C.F., Raviña E., Centeno N.B., Carotti A., Loza M.I. J. Med. Chem. 45:2002;54-71.
15. Hathaway B.A., Nichols D.E., Nichols M.B., Yim G.K.W. J. Med. Chem. 25:1982;535-538.
16. Yamaguchi T., Yanagi T., Hokari H., Mukaiyama Y., Kamijo T., Yamamoto I. Chem. Pharm. Bull. 46:1998;337-340.
17. Barloco, D.; Cignarella, G.; Giardina, G. A. M.; Grugni, M.; Ronzoni, S. WO 0027815. CAN 132:347490.
18. Bianchi D., Cesti P., Battistel E. J. Org. Chem. 53:1988;5531-5534.
19. s)]. See: Chen C.-S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294-7299.
20. Job A., Janeck C.F., Bettray W., Peters R., Enders D. Tetrahedron. 58:2002;2253-2329.
21. Djuric S.W., Docter S.H., Yu S.S., Spangler D., Tsai B.-S., Anglin C.P., Gaginella T.S., Kachur J.F., Keith R.H., Maziasz T.J., Villani-Price D., Rao T.S., Walsh R.E., Widomski D.L., Fretland D.J. Bioorg. Med. Chem. Lett. 4:1994;811-816.
22. Herold P., Herzig J.W., Wenk P., Leutert T., Zbinden P., Fuhrer W., Stutz S., Schenker K., Meier M., Rihs G. J. Med. Chem. 38:1995;2946-2954.
23. 1H NMR spectroscopy, each hydrazone was pure from the other diastereomeric hydrazone.
24. Enders D., Hundertmark T., Lazny R. Synlett. 1998;721-722.
25. Doulut S., Dubuc I., Rodriguez M., Vecchini F., Fulcrand H., Barelli H., Checler F., Bourdel E., Aumelas A., Lallement J.C., Kitabgi P., Costentin J., Martinez J. J. Med. Chem. 36:1993;1369-1379.
26. Cohen S.G., Milovanovic A. J. Am. Chem. Soc. 90:1968;3495-3502.
27. Lerch, U.; Jendralla, J.-H.; Seuring, B.; Henning, R. EP 0512415. CAN 119:27835.
28. Flack H.D. Acta Crystallogr., Sect. A. 39:1983;876-881.
29. Bernardinelli G., Flack H.D. Acta Crystallogr., Sect. A. 41:1985;500-511.